First Time
by QueenBee7
Summary: Sexual exploration with Chuck and Blair... Chuck obviously knows what he's doing, and of course we know what happens to Blair's virginity, but what if her first time with everything beyond kissing was with him too? Set some time in Season 1, pre limo sex.
1. Chapter 1

**A/N: Okay, so basically the premise of this story is that Blair experiences her first time with everything other than making out with Chuck. This doesn't include the first time they have sex, because we all know how that one turns out. But all other kinds of sexual foreplay are included, so enjoy. As for my other story, Finding a Way Back, I promise I'll add to it again eventually... it's been a busy month, but I should have more time to update once I'm home from school next week. This story just sort of occurred to me out of nowhere, so I decided to go for it. I hope you like it... please read and review!**

First Time

Blair glanced over at the clock sitting on her bedside table. 11:30. Perfect. That meant her mother had already been asleep for half an hour, and that Dorota was just turning in for the night. She would not be disturbed until Dorota woke her for school at 7:30 the next morning.

Blair was lying on her bed, propped up against her pillows and not yet under her covers because it was a warm night. She was wearing her favorite pale green slip, the one that always made her feel sexy. Or at least sexier than she ever felt when she was around Nate. She loved Nate - well, she was pretty sure she did, anyway - and she knew he was her golden prince, her happily ever after. But at the same time, she couldn't help but notice that when he looked at her, their was never any desire in his eyes. In fact, it always seemed like he was more enthralled by Serena than by Blair - as if Blair didn't already have enough of an inferiority complex as Serena's best friend. All she wanted was for a man to look at her with lust in his eyes, to throw her against the wall and whisper dirty words in her ear and ravish her. The problem was, she knew Nate would never do that. The even bigger problem was that she wasn't sure she even wanted Nate to be the one who did that to her.

Blair wanted to be touched. _Really_ touched. But not by Nate. For some mysterious reason that probably involved the universe conspiring against her, Blair could tell that even if she and Nate ever did more than make out (which, up to this point, they hadn't), Nate would not be able to touch her the way she wanted to be touched. And so she had resorted, without much success, to doing it herself.

It was not something she was proud of. It was her darkest, dirtiest secret, and she felt embarrassed every time she slid two fingers inside herself and tried to make herself feel the kind of pleasure Serena had always described. But at the same time, she desperately wanted that incredible feeling, whatever it was, and she refused to stop trying until she felt it. And so at 11:30 each night, she allowed her hand to trail down her stomach, slide into her panties, and begin rubbing circles around her clit. It felt good, and a few times she swore she had nearly orgasmed. But, much to her frustration, it had never actually happened.

Tonight was no different. As her fingers worked her core, she could feel the tension building in her body, but she could already tell it wasn't going to work. With an angry sigh, she kept pushing her fingers in and out, around and around, feeling almost desperate. And then she heard a familiar voice, and her heart nearly stopped.

"Well, well. I think I may have just died and gone to heaven," Chuck drawled, the signature smirk on his face mixed in with an expression of awe, and, unless Blair was very much mistaken, lust.

Blair flushed crimson red and hurriedly pulled her fingers out of her panties. "Chuck! What the hell are you doing here?! Get out!" she hissed, not wanting to wake the rest of the house.

Chuck merely smirked and strode across the room so that he was standing beside her bed. "I _was_ stopping by to share with you the latest dirt my PI uncovered regarding Penelope's... ah, _extracurricular_ activities with her flute instructor. Let's just say that she is most definitely playing his instrument. But enough about that... it seems that God had much greater plans for me tonight." He reached forward to stroke her cheek, but Blair slapped his hand away.

"Haven't you ever heard of knocking? And since when do you believe in God?" Blair said angrily, pulling a pillow across her chest to serve as a barrier between her and Chuck.

"Since I walked into your room and discovered Blair Waldorf, the virgin queen, all hot and bothered and trying to get herself off." He sat down on the bed and leaned towards her. "What's the matter, princess? Nathaniel not satifsying your needs? I always knew you were too much for him." It was true. Chuck had stifled his attraction to Blair for years out of respect for both her and his best friend, but he had always known that Blair deserved so much better than Nate. She was, after all, the most exquisite thing Chuck had ever seen, but stupid Nathaniel was always too busy gazing longingly at Serena to notice what was right in front of him. It infuriated Chuck to no end, but he had kept that to himself because he thought Blair was happy. Now it seemed that she had finally realized there was something missing in her perfect relationship with Nate. And the fact that she had resorted to touching herself - well, that was essentially Chuck's greatest fantasy come to life. He had nearly come in his pants just watching her.

Blair didn't know whether she should feel more scandalized or mortified. Both seemed like appropriate reactions to having Chuck Bass walk in on her masturbating, but in an effort to preserve her dignity, she opted for scandalized. "You're disgusting. Of course Nate is satisfying my - needs. Not that it's any of your business."

"I'm Chuck Bass. Everything is my business," Chuck said. "Besides, you forget who you're talking to. Nathaniel is my best friend. He has no idea how to touch a girl. And even if he did, I know he's not touching you. If he were, you wouldn't lying in bed alone finger-fucking yourself at 11:30 on a Wednesday night. Not that I'm complaining."

Blair opened her mouth to retort, but she couldn't think of anything. Finally, she settled for a threat. "If you ever speak a word of this to anyone, including Nate, I will personally see to it that every female in Manhattan hears that you have been mysteriously afflicted with a highly contagious and untreatable case of genital herpes."

Chuck sneered. "Be my guest. I could use a bit of a challenge. And it's not as if I'm opposed to calling in foreign company."

"You're heinous," Blair snapped. "So then what? Are you going to tell the whole school about this?"

"Please," he scoffed. "What would be the point in that? I'd rather keep this mental image for my own personal enjoyment."

"Pervert."

Chuck smirked again. "I do have a proposal for you, however."

Blair raised her eyebrows. "And what's that?"

"Let me show you what it feels like to be fingered well." Chuck watched her face closely as he spoke, wondering if this was pushing her too far. He of course knew she would reject him instantly, but it was worth a shot. Especially considering the uncomfortable state of his groin right now, touching Blair Waldorf was something he wanted very badly.

"No," Blair said automatically, even as the idea of Chuck fingering her sent a thrill through her whole body. It was disgusting. DISGUSTING, Blair. But at the same time, it was intriguing. And so deliciously forbidden. She wanted it - wanted him. She loved the way he was looking at her right now, his eyes dark with lust. Their bodies were so close... if he just moved a little bit closer, they'd be touching. He'd be touching her. _Really_ touching her.

"Fine," Chuck said, trying to hide his disappointment. "I'll see you tomorrow, Waldorf. Thanks for the show."

Just as he rose to leave, Blair caught his hand. His heart leapt. "Chuck. Wait. I-" His eyes flashed back to hers, and he understood. She was too afraid to ask for what she really wanted, so she was silently begging him to give it to her anyway. She tugged on his hand a little, and he leaned in, his lips hovering inches from hers, completely unable to breathe. And then he kissed her, and it felt as if something had exploded inside both of them.

He was on top of her in seconds, pressing her down on the bed and sliding his tongue into her mouth as she kissed him back eagerly. She had never been kissed like this before - with so much passion and urgency. It was as if Chuck couldn't get enough of her. His hand ran up her creamy thigh and under her slip, coming to a halt on her butt. He pulled her into him, and her leg hooked around his back. His other hand found its way to her breast, kneading it through the fabric of her slip. He allowed his mouth to drift down her body, leaving kisses on her jaw and collarbone before pulling down the strap of her slip and pressing his lips to her breast. Blair let out a slight gasp and knotted her fingers in his hair as his tongue glided over her nipple. She couldn't believe that she was actually doing this right now - with Chuck Bass, of all people - but it felt so good and so right that she never wanted to stop.

But then she felt his hardness pressing against her, and she flinched, suddenly scared. Chuck pulled away and their eyes met. She was surprised to see concern in his expression. "What's wrong?" he asked.

"It's just - I - nothing," she stammered, embarrassed.

"Blair," he pressed.

"Never mind. I'm fine."

"_Blair_." His eyes bored into hers, demanding that she tell the truth.

"I - I'm scared," she admitted, looking away from him.

"Of me?"

"Kind of," she said, blushing. "And just all of this."

"I'm not going to hurt you," he said softly.

"I know."

"And you can stop me whenever you want. I won't get mad."

Blair nodded, still not meeting his gaze.

"Hey. Look at me," he said, lifting up her chin so that their eyes met again. Blair was again surprised by how genuinely concerned he looked. "Are you okay?"

"Yeah. Yes."

"It's going to feel amazing, Blair. Trust me." _Trust me_. Hearing him say those words was oddly comforting. Blair hated (or pretended to hate) a lot of things about Chuck - like how he was disgusting, cocky, and morally bankrupt, to name a few - but in spite of all that, she had always trusted him.

"Okay," she said, her voice more confident. "Keep going."

Chuck grinned. "You sure?"

"Yes," she said, smiling back.

Chuck kissed her again, this time more softly. He wanted to make her feel comfortable by taking it slow. He also wanted to savor every single moment of what was happening to him right now, because only in his wildest dreams had he ever hoped he would really be touching Blair Waldorf.

Blair tentatively would her arms around her neck and pulled him in closer, deepening the kiss as her tongue delved into his mouth. Chuck slid a hand between her legs, massaging the soft skin of her inner thighs as he inched towards her center. When he finally reached her panties, he was both surprised and pleased to find that they were already damp. He hooked a finger through the strap and pulled them down, then returned his hand to its position between her legs. He heard Blair's breath catch in her throat as he slowly traced a finger across her slit. Chuck couldn't believed how hot and wet she was already, and the fact that it was all because of him turned him on even more.

"You're so wet," he murmured against her lips, his fingers hovering infuriatingly close to her aching center.

"Mm," she replied. "Touch me, Chuck."

The hint of desperation and the breathiness in her voice was all the incentive Chuck needed. Looking her straight in the eye, he gently slid two fingers into her and began slowly pumping them inside of her. Blair let out a cry, lifting her hips up against his hand. She couldn't believe how good this felt. And then he began to pick up the pace, and he brought his thumb up to circle her clit. Blair fisted her hands in her sheets and began to moan in earnest, arching off the bed, desperate to feel him deeper inside her. Chuck watched her face in fascination, absolutely transfixed by this new side of Blair that he had always known existed but had never actually seen.

Blair felt her body begin to clench, and then, before she knew it, she was shaking and screaming Chuck's name as she rode out her first orgasm against his hand. When it was over, she looked up at him, panting, a slightly dazed expression on her face. "Wow," was all she could manage to say. It had been even better than she expected, and although she would never admit it to him, she suspected that had something to do with the fact that it had been Chuck fingering her.

Chuck smirked, feeling very satisfied with himself and more than a little turned on. "Told you."


	2. Chapter 2

**A/N: Okay, sorry it took me so long to update this story! I'll try to get the next chapter up sooner. Just to clarify, this is set some time at the beginning of season 1, before Chuck and Blair have sex. The idea is that Blair is still with Nate, but she's beginning to doubt their relationship, especially because of what happened with Serena. Basically I just wanted to write about what it would be like if Blair experienced all of her sexual firsts with Chuck. So that's what this is. There will probably be 2 more chapters after this one... Oh and also, let me just say that the Chuck and Blair scenes in the finale (especially the last one) absolutely made my life. I'm so happy he finally said it!!!! I LOVE THEM. The only thing that was missing was some very steamy Chair sex scenes, but hopefully we'll get more of that next season. And speaking of next season, I don't know how I'm going to last all summer without new episodes! I suppose I'll just have to immerse myself in writing Fanfiction :). Okay, now I'm done ranting. Please read and review!**

First Time Chapter 2

As Blair lay panting in something of a post-orgasm daze, Chuck rolled on to his back beside her and debated what to do about the increasingly pressing need in his groin. Fingering Blair and watching her orgasm because of him had made him hornier than he had ever been in his entire life, and he needed some release as soon as possible. Of course, ramming his dick into Blair would have been the best solution to his problem, but seeing as that wasn't going to happen any time soon, he needed an alternative. Normally, he would have gotten whatever slut he was with to blow him, but Blair was different - she was his friend, and he respected her. He didn't want to ask her to do anything that made her uncomfortable. He supposed that if he had to, he could go jerk off in her bathroom or something, although he wasn't entirely sure that would work.

"Chuck?" Blair said after a few minutes of silence.

"Mm?" Chuck replied, shifting slightly in an effort to relieve some of the discomfort in his groin.

"Thank you," she said quietly.

Chuck let out a small laugh. "Any time, Waldorf. I'm happy to help whenever your needs need satisfying."

They lay in silence for another minute or so, Chuck growing more and more uncomfortable.

"Chuck?" Blair said again. She had suddenly been struck by an idea that was simultaneously terrifying and thrilling.

"Yes?"

"What about your needs? Could I maybe give you a hand?" Blair smirked to herself, pleased with her little play on words.

Chuck looked over at her, eyes wide. "Are you serious?"

Blair propped herself up on her elbow and nodded. Her heart was beating very fast, but she was pretty positive she wanted to do this. She wanted to give Chuck the same kind of pleasure he had just given her. "Completely."

Chuck watched in awe as she reached over and pulled his shirt out his pants, then began working on his belt. She had it off quickly, and before he knew it, she had pulled down his pants and boxers, exposing him. He was pleased to see her eyes widen and her lips part slightly when she saw how big he was. "Umm," she said, her voice trembling slightly. "How -"

"Wrap your hand around me, Blair, and just move up and down," Chuck instructed. She did as she was told, tentatively wrapping her fist around the base of his penis. His breath caught in his throat at the feel of her hand on him. She slowly began moving up and down, taking it as a good sign that Chuck's breathing was getting heavier and heavier. Emboldened by the way he was responding to her, Blair decided to play with him a bit. She traced a finger over his balls, then ran it up the underside of his penis. Chuck gasped as she began to massage the head with her palm.

"Fuck - Blair - up and down, like I told you," he grunted, his hips arching towards her. Blair merely smirked wickedly and began devising a scheme to torture him. After leaving a few kisses on Chuck's neck, she temporarily abandoned his throbbing dick and redirected her attention to completing removing his pants, which had thus far been around his knees. She tugged them all the way off and tossed them to the floor, then climbed on top of Chuck, straddling his right leg. She ground her bare, still wet pussy against his thigh, causing his eyes to roll back in his head.

"Jesus Blair, stop messing around and put your fucking hands on me!" he moaned. His cock was painfully hard by now. How was Blair, the untouched virgin, so damn good at torturing him? It was like the girl had been specifically designed to drive him absolutely out of his mind.

"Only if you ask nicely," Blair purred, making him flinch as she allowed her fingertips to graze over his tip.

"Please," he groaned, and he felt her small, warm hand close around the base of his penis once more. "FUCK, _please_!" She started working her hand up and down again, varying the pressure she applied and gradually picking up the pace. Chuck could feel himself getting closer and closer, he was nearly there... "Shit - Blair - move - I'm about to come -" he choked out.

"It's okay, I don't care," she replied, and seconds later, he exploded on to her stomach. The normal Blair would have been completely grossed out, but the post-being-fingered-by-Chuck-Bass Blair was so thrilled to have successfully jerked him off, and so turned on by the fact that she had literally had him - Chuck _fucking_ Bass - begging her to touch him, that she really didn't care that much.

"Sorry," Chuck said, grabbing some tissues from her bedside table and using them to clean her up. Blair was pleased to feel that he was still trembling in the wake of his orgasm.

"It's fine," she replied honestly. "So, how'd I do?" she asked with a smirk as Chuck tossed the tissues into the trash.

Chuck looked at her, still unable to believe that Blair Waldorf had just given him the best orgasm he had ever had in his life - and they hadn't even had sex. She looked so beautiful right now, her eyes bright, her cheeks flushed, her hair a bit messy, and her body still gloriously naked. She was more free and uninhibited than he had ever seen her before. Why she had chosen him of all people to show this side of herself to, he had no idea, but he wasn't about to complain about it. He only hoped that this would be more than a one time occurrence. "You were incredible," he said, and Chuck didn't think he had ever answered a question more sincerely in his entire life.


	3. Chapter 3

**A/N: Okay, sorry it took me so long to get this next chapter up! And also sorry that there's no rated M action in it! Originally, there was going to be stuff in this chapter, but then it was taking so long to write that I decided to just put this part up as a sort of intermediate chapter. I'm going to try really hard to get the next chapter (which will most definitely be M) up soon, but in the mean time, I wanted to post something since it's been taking so long... I hope you enjoy! Please read and review :)**

Chapter 3

At some point following what Chuck would always remember (and occasionally refer to) as the-most-epically-amazing-hand-job-ever, he and Blair fell asleep beside each other in her bed. Fortunately, Blair awoke around 4 in the morning and realized that Dorota would probably not be pleased if she were to discover Blair and a boy who was not her boyfriend naked in her bed. Chuck was shocked out of a very pleasant dream (he couldn't remember all the details, but he was pretty sure it involved a scantily clad Blair and large amounts of whipped cream) by Blair slapping him and hissing that he better get lost fast.

"Blair, it's 4 o'clock in the morning," Chuck said groggily. His hair was sticking up at various odd angles, and much to Blair's chagrin, she couldn't help noticing that he looked absolutely adorable.

"So? I need to wake up for school in three and a half hours, and if Dorota finds you here, it won't be pretty," Blair whispered, throwing his pants at him.

"I can think of much better ways to spend the next three and a half hours," Chuck drawled, still not moving.

"If you aren't out of my bed 30 seconds from now, you'll be spending them in the ER," Blair hissed.

"Mm, someone's feisty this morning," Chuck said with a smirk. "I like it."

Blair grabbed Chuck's upper arm, sinking her nails into his flesh. "Ow!" he cried, trying to pull away, but her grip was too firm.

"Out. _Now_," she snarled before letting go of his arm.

"Fine," he replied, rubbing his arm as he rolled out of her bed. He pulled his boxers and pants on while Blair looked pointedy in the other direction. He was halfway through buttoning up his shirt when she finally spoke again.

"No one can find out about last night. Ever," she said. "Especially not Nate."

Chuck felt an odd twinge in his stomach at the mention of Nate. Right. Nate. His best friend. Blair's boyfriend. Who she was still dating for some unknown reason. _Shit_. Chuck managed a smirk as he said, "Don't worry princess, my lips are sealed. But I wouldn't mind a repeat of last night the next time you're feeling... _unsatisfied_."

Blair glared at him. "You wish, Bass."

"Please, Waldorf, are you really going to waste your time pretending you didn't enjoy last night just as much as I did?"

The fact that Blair knew he was absolutely, 100% right about how much she had enjoyed last night made the look on her face even more murderous. "You can go now, Chuck," she said in as calm a voice as she could muster.

"It's been a pleasure," he said, that infuriating smirk still on his face. "See you in school." And with that, he sauntered out of the room, leaving Blair to contemplate the events of last night. She knew she should be feeling guilty and disgusting, but all she could think about was Chuck kissing her, Chuck touching her, Chuck - the great Chuck Bass! - squirming and panting because of what she was doing to him. Never, in all the years she had spent with Nate, had she ever felt as desired as Chuck had made her feel last night. Never had she felt so electrified, so _alive_. And she had most certainly never before felt pleasure that came anywhere close to what she had experienced with Chuck. As much as she hated to admit it, it had been a truly incredible night - and whatever she may have said to him, she was just as eager as he was to repeat it. Ugh. This was shaping up to be quite a dilemma. Deciding she would deal with it in the morning, she rolled over and went back to sleep, trying unsuccessfully to stop images of last night from racing through her head.

* * *

The next morning before school, Blair was seated in her usual spot on the steps outside of Constance, holding a yogurt but not really eating it. Penelope and the girls were assembled around her, chatting about the latest gossip and mercilessly dissecting the outfits of their classmates. Nate was sitting beside Blair, his hand resting on her stocking-clad knee, but as usual he seemed more interested in talking to Serena than to Blair. The only thing that made today different from any other day was that Blair was not doing everything in her power to keep Nate's attention focused on her rather than Serena. In fact, she found herself much more preoccupied with thoughts of a certain dark-haired, dark-eyed boy than with concerns about her boyfriend's perpetually wandering eye.

Try as she might, Blair could not shake the thought of Chuck from her mind. Even more alarmingly, she had become consumed with a burning desire to see him again - to feel him again. Unfortunately, she didn't know when - or if - another opportunity to be with him would present itself. Furthermore, she couldn't help but wonder whether he would even want to do anything with her again, especially if she wasn't going to have sex with him. Chuck was notorious for his hit-it-and-quit-it mentality: he made a point of never sleeping with the same woman twice. But he had said last night that he wouldn't mind a repeat... Had he just been toying with her, or had he meant what he said?

As she fretted over this, Blair realized her life had sunk to an all-time low. Agonizing over _Chuck Bass_? This had to be a sign of bad things to come...

* * *

Unbeknownst to Blair, Chuck had been watching her from his limo's spot across the street for most of the morning. He had been torn between disgust with himself for acting like a pathetic, lovesick stalker and a strange, overwhelming desire to see what Blair was doing, but the latter had ultimately won out. As he watched her, he couldn't help but notice that she seemed less interested in Nate than usual - or was he just imagining it? And more importantly, why did he care? Chuck Bass didn't deign to care about girls. And yet, if the irritating fluttering in his stomach was any indicator, it seemed that he cared about this one.

Glancing down at his watch, Chuck realized it was nearly time to go to class. He slid out of the limo and walked through the entrance gates, allowing himself one last look at Blair. To his surprise, she was looking back at him. Their eyes met, and Chuck felt a new wave of fluttering in his stomach. Rather than looking away or shooting him a nasty glare, as he had expected her to, Blair simply stared at him, her gaze smoldering. She finally looked away to pull out her phone and send a text, smirking slightly as she typed. Then she turned and ascended the steps without so much as a backward glance at Chuck.

He was watching her walk away when he felt his phone vibrate in his pocket. Flipping it open, he saw that he had a new text from Blair:

Lunch? Breakfast left me a little... unsatisfied.  
-B

Chuck was surprised he didn't get a boner on the spot. Hands shaking slightly, he typed a message back:

My limo. 12:00.  
-C

**Okay sorry this is so short/not the best thing I've ever written... I was having a lot of trouble turning my ideas into writing. The next chapter will be up soon!**


	4. Chapter 4

**A/N: Okay, I have to say I'm extremely proud of myself for getting this chapter up so soon after the last one... all of your reviews were such great motivation! Hopefully I'll be able to keep up with posting more regularly from now on. Anyway, I'm really happy with how this chapter turned out, and I hope you all enjoy it too! As always, please read and review :)**

Chapter 4

Blair glanced up at the clock on the wall of her Pre-Calc classroom for what felt like the 100th time that day. 11:57. Three minutes until lunch. With Chuck. In his limo. "Lunch" with _Chuck_ in his _limo_. Blair still couldn't believe she had gotten up the nerve to send him that text this morning. But when she had seen him looking up at her on the steps, unmistakable lust in his eyes, it was as if something had clicked in her head. Fuck Nate. He could go screw Serena again for all she cared, because she had finally realized that he couldn't give her what she needed. Chuck could. It was as simple as that.

11:59. One minute. Blair felt slightly sick to her stomach with anticipation. She slid her binders and books into her bag, ready to sprint out of class and discreetly slip into Chuck's limo before the rest of the school (particularly Nate) could come outside and see who she was spending her lunch break with.

12:00. The bell sounded. Blair was on her feet and striding out into the hallway before the rest of her classmates had even begun to get their things together. She hurried through the empty courtyard and down the steps, her stomach lurching as she spotted Chuck's limo across the street. By the time she had crossed the road, Chuck's chauffeur was holding the door open for her. She thanked him and slid inside.

"Waldorf," Chuck said, wearing his trademark smirk as he nodded at her in greeting.

"Bass," Blair replied.

They stared at each other for a while, each wondering what the other was thinking. Finally, Blair broke the silence.

"No one can know about this, Chuck."

"Deal."

And with that, he grabbed her around the waist, pulled her on to his lap, and kissed her. Blair responded eagerly, her lips parting to accept his tongue. His hands were in her hair, and hers were fumbling with the buttons of his shirt. When she had finally unbuttoned all of them, he shrugged out of the shirt, and Blair tossed it to the floor the limo. Chuck reached under her skirt and took hold of the band at the top of her thigh high stocking. Pushing her back on to the seat, he slid down to the floor, placed her calves on his shoulders, and proceeded to slowly roll each of her stockings off of her legs. Then he looked up at her, a wicked glint in his eye.

"So Blair, why did you want to meet for lunch today?" he asked, rubbing her legs.

"I told you, breakfast left me feeling extremely unsatisfied," she replied. She hoped Chuck couldn't hear how loudly her heart was beating.

"Mm... is there anything I can do to help you reach your desired level of satisfaction?"

"I think doing exactly what you did last night might do the trick."

"Might I suggest something even better?"

Blair's eyes widened with fear. "Not --"

"No, Waldorf, not sex," he said. "Calm down."

"Then what?" she asked, her expression of fear was replaced with one of puzzlement.

He smirked, pleased with her naivete. It would be so much more enjoyable to watch her experience something that she wasn't expecting. "Just relax," he said reassuringly. "I'm about to take you to a realm of pleasure that will have you screaming my name even louder than you were last night."

"I was not _screaming_," Blair cried indignantly.

Chuck raised his eyebrows.

"Okay, fine, maybe a little," she admitted.

He blinked at her.

"_Fine_, a lot. Satisfied?" she said huffily.

"Not as satisfied as you're going to be."

He grabbed her by the hips and pulled her closer to him, then began tugging her shirt out of her skirt. She shivered as he pressed a few kisses to the soft, exposed skin of her stomach. He folded up her skirt and slid her panties off before gently placing his hands on her thighs and spreading her legs wide. Blair squirmed slightly; the way he was staring hungrily between her legs made her feel slightly uncomfortable, and she still wasn't even sure what he was going to do to her.

"Chuck --" she began.

"Shhhh," he said, and the feeling of his hot breath against her wet center made her shut up. He licked his way up her inner thighs, his mouth getting dangerously close to where she was desperate to feel him. And then, suddenly, he was licking her folds and sliding his tongue inside of her.

"Oh - my - God," Blair breathed. She had certainly not expected this. It was a level of pleasure unlike anything she had ever experienced. He was sucking, licking, doing things to her with his tongue that made her arch off the seat and dig her heels into his back. And then she felt his thumb begin to rub fast circles around her clit, and just as he had predicted, she screamed his name, all sense of sanity and control completely lost.

Chuck had always assumed that he would never actually enjoy giving a girl head. It was just a chore that he would occasionally perform if he knew it would get him a blow job in return. But giving head to Blair was shaping up to be one of the more enjoyable sexual experiences of his life. The way she responded to his every touch made him more and more eager to please her. To know that he was the one to drive her nearly insane with lust and pleasure, that she was trusting him to do this to her instead of Nate, was an incredible turn-on. And then, when he heard her screaming his name - well, that made him feel like he could do this for hours and still enjoy every second of it.

He could tell that she was getting close. She had knotted her fingers in his hair and was pulling him closer, allowing his tongue to delve even deeper inside of her. Still rubbing her clit with one thumb, he used his other hand to cup her ass and press her even harder against his mouth. She was whimpering, her breathing staggered, she could feel her body begin to tense up again... and then an orgasm even more mind-blowing than the one last night ripped through her, and she came as his name fell from her lips one last time.

Feeling very pleased with himself, Chuck licked the cum off her thighs before sliding her panties on and folding down her skirt. When he had done this, she was still sitting there limply, and so he began to roll her stockings back up her legs. Just as he finished putting on the second stocking, she spoke.

"We need to do this more often," she said.

He smirked. "Enjoyed that, did you Waldorf?"

"Nah," she smirked back. "Looks like you didn't enjoy it much either," she added, looking down at where his erection was pressing very conspicuously against his pants.

"Not at all."

Blair placed her hand over his bulge and was just reaching for the zipper of his pants when her cell phone vibrated. Flipping it open, she saw that she had a text from Serena:

Where are you? Class is about to start!  
-S

Blair glanced at her watch and saw that, indeed, lunch was over and class would be starting again in approximately 45 seconds. "Fuck! I'm going to be late!" she cried, grabbing her bag and hurriedly sending Serena a reply:

Coming now!  
-B

Chuck caught her hand as she reached for the door handle. "Blair, you can't leave me like this!" he said angrily, gesturing at his crotch.

"I can't miss _class_!" she said, looking scandalized at the thought. "I'm sorry, I'll make it up to you later, I promise..." and with that, she slid out of the car and dashed across the street. Chuck watched her go with his mouth slightly open, feeling furious that she had left him to deal with this on his own. As if he would be able to, now that he knew what it felt like to be touched by Blair Waldorf. But his anger was slightly abated when he remembered what she had said as she got out of the car - "I'll make it up to you later, I promise..." He had a sneaking suspicion that Blair's version of making things up to him was going to be well worth the wait.


	5. Chapter 5

**A/N: Okay, first of all, I would like to say SORRY SORRY SORRY for taking so long to upload this chapter! I've had it mostly done for at least 3 weeks, but I was having trouble figuring out how to end it, and then I've just been busy with work and vacation. But anyway, here it is! Finally! I hope you all find it enjoyable enough to make up for the wait :). This is the last chapter of this particular story... I decided not to include their first time having sex because I like the way it happened on the show, but I don't think it makes sense with this story. So I hope you all enjoyed this! Thank you soooo much for reading, and I promise I will be adding new chapters to my other story, Finding A Way Back, and starting new stories as well (eventually)! Again, thanks for being patient with me. Please read, review, and enjoy!**

Chapter 5

Blair rushed into class just as the bell rang, her face flushed and her headband askew. She sank into a chair and whipped out her notebook as Serena shot her a curious sideways glance.

"Where were you?" she muttered.

"I had to pick something up at home - lost track of time," Blair lied, avoiding her best friend's gaze. Luckily, Serena didn't have time to question her any further because at that moment, their teacher began speaking.

Blair found it excessively difficult to sit through English and the rest of her classes that day. How was she supposed to focus on books and verb tenses and centripetal force when the memory of Chuck with his mouth down _there_ was still fresh in her mind? More importantly, why would she ever want to focus on anything else when she could instead be reliving every single second of the time she had spent in his limo? And then, of course, there was the distraction of what she was planning on doing to Chuck as an apology for abandoning him earlier...

By the end of the day, Blair had become convinced that the clocks in Constance moved significantly slower than was natural. After what felt like several years, the final bell rang, and Blair had to force herself not to run flat-out to her locker. She was just resetting her lock, ready to make a speedy escape, when Serena appeared beside her.

"Hey B! Where are you off to in such a hurry?" Serena said brightly.

Blair resisted the urge to snap at Serena, and instead plastered a smile on her face. "Just home. Lots of work to do, you know." She heaved what she hoped was a convincingly exasperated sigh.

"Oh, right... do you think you could spare half an hour for coffee? Nate was just saying earlier how he thought the three of us should hang out after school."

As if on cue, Nate strode up behind them and slid his arm around Blair's waist. It was a small gesture of affection that Blair usually adored, but today she found it to be more irritating than endearing. Perhaps that was because the feel of Chuck's fingers pressing into her hips still seemed to be lingering on her skin, almost as if he had burned her. "So are we going for coffee?" Nate asked.

"I'm sorry, but I really don't think I have time," Blair said, feigning disappointment as she shrugged out of Nate's arm. "You two go without me though. I'll see you tomorrow!" She pecked Nate on the cheek and then hurried off, leaving a mildly suspicious Serena and a clueless (as usual) Nate in her wake.

* * *

After his lunchtime rendezvous with Blair, Chuck had decided to take the rest of the afternoon off. It had taken him the greater part of an hour to get himself off after she had left him like that, and to his great annoyance, he had only been successful once he started replaying everything that had happened between him and Blair in the past 24 hours over in his head. He particularly enjoyed recalling how her small hand had felt wrapped around his dick, and the expression on her face when he had first touched her, and the way she had looked after she orgasmed, and the way she had squirmed beneath his touch in the limo, and the way she had screamed his name as she came... okay, fine, if he was being honest, he particularly enjoyed recalling all of it.

Chuck was now seated on the couch in his suite, sipping on a scotch and brooding. It bothered him how desperately he wanted to see her again. She was just a girl, after all. But as that thought crossed his mind, he realized how far from the truth it was. Blair Waldorf would never be "just a girl". She was the most fascinating person Chuck had ever encountered: exquisitely beautiful, poised, elegant, pure, capable of controlling virtually everything and everyone around her. She was undeniably a bitch, but she was also a loyal friend to Serena and a devoted (up until recently, at least) girlfriend to Nate, the two people who were perhaps the least deserving of her dedication. And then, beneath that cold, flawless exterior, there existed a vulnerable, passionate girl that no one had ever seen. That is, until Chuck had come along and found a way to draw that girl out.

As he reflected on the enigma that was Blair Waldorf, Chuck heard a knock on the door. Praying it wasn't Nate (he didn't think he could handle being around his golden boy of a best friend at the moment, especially now that he had gotten Blair off more times in the past 24 hours than Nate had in their entire 11 year long relationship), he strode over to the door and opened it cautiously. To his surprise, he found Blair standing in front of him, still dressed in that sexy little school uniform, a determined look on her face.

"Hello, Chuck," she said in what was clearly supposed to be a confident voice. "Can I come in?" She walked past him and into the suite without waiting for his reply.

"What are you doing here?" he said, closing the door. It came out more coldly than he had intended, but he was still pretty pissed at her for earlier.

Blair tried not to let the edge in his voice bother her. "I told you I'd make it up to you when I left you in the limo earlier," she replied.

"Yeah, well, I don't really feel like doing anything with you right now," he said, wondering as he spoke why he alway had to be such an asshole about things.

Blair snorted. "Since when?" She never took any of his shit. It was one of his favorite things about her, although he wasn't going to admit that right now.

"Since you let me give you the best orgasm of your life and then proceeded to go to fucking _class_ while I was left _alone_ with a fucking boner," he spat.

"Oh please Bass, stop being such a bitch about it," Blair scoffed. She pushed him down on to the couch and straddled him, settling her ass on his crotch, which, naturally, had already begun to harden. "Now just keep your mouth shut so I can keep my promise and make it up to you. I have a feeling you're going to like this." Then she pressed her lips to his, and all of his anger seemed to melt away. Blair Waldorf was kissing him again, and that was really the only thing that mattered right now.

"I have a feeling you're right," he murmured, and he felt her smile against his lips. He slid a hand around to the back of her head and kissed her more fervently as she began to loosen his tie. "So, how are you planning on repaying me?" he asked when her mouth left his to plant kisses on his jaw and neck.

"You'll see," she said mysteriously, kissing his chest as she unbuttoned his shirt. She ground her hips against his crotch, smiling to herself as she heard his breath hitch. He grabbed her hips and pressed her down on his erection, and she whimpered a little as she felt his hardness against her core. It would feel so wonderful to just stay like this, rubbing herself against him, but Blair was on a mission to repay Chuck for this afternoon, and this was not how she wanted to do it.

Chuck gave a groan of disappointment as Blair slid off his lap, but when he saw that she was now kneeling on the floor between his legs, his disappointment subsided considerably. Smirking up at him, she undid his pants and pulled them down around his ankles. Then she ran her fingers up his calves and thighs, sliding a hand under his boxers and just grazing his throbbing penis. Chuck rested his head back against the couch and closed his eyes, preparing himself for the paradise that was Blair Waldorf's hand wrapped around him. He felt her tug down his boxers and take him in her small hand. And then she felt her breath against his tip.

"Open your eyes, Chuck," Blair purred.

His eyes snapped open just in time to witness what was perhaps the most erotic thing he had ever seen. Blair's lust-filled eyes were locked on his, and she was closing her perfect pink lips around his tip. Dear _God_. Chuck watched her, fixated, as she eased his length deeper and deeper into her warm mouth at an agonizingly slow pace. Then she pulled it back out and smiled wickedly.

"Did you like that, Chuck?"

He nodded numbly, watching as she absentmindedly massaged his tip with her thumb.

"Do you want me to do it again?"

"Fuck. Yes," he managed to say, and seconds later, he was engulfed in her mouth again, and she was sucking him off in earnest.

It was ecstasy. Chuck had received many blow jobs in his 16 years, but none of them had ever compared to this. As if the way she was sucking and licking him wasn't incredible enough, knowing this was Blair's first time, and that she actually wanted to have his dick in her pure, virginal mouth, was just about the biggest turn-on ever.

She shot him a sultry look before pulling her lips off of him and running her tongue up the base of his shaft. Then she took him in her mouth once more, swirling her tongue around his length as she gently grazed his balls with her fingernails, causing his hips to buck upward off the couch. He could feel himself getting closer, and he grabbed her head, pushing himself deeper into her. Blair accepted him eagerly, relishing the high she got from giving him so much pleasure.

Chuck felt his self-control slipping away rapidly. "Blair-" he choked out in an attempt to warn her, but even as he spoke, he couldn't help but knot his fingers more tightly in her hair. When he exploded into her mouth, she swallowed obligingly before tucking him back into his boxers and kissing her way up his chest.

"So are we even?" she asked innocently, settling herself on the couch beside him.

"I'd say so," Chuck panted.

"Good."

Blair looked down, unsure of what to say or do now. She noticed that her hand was resting beside Chuck's, their fingers just barely touching. She snuck a glance at him, and saw that he was looking at their hands too. Slowly, and so imperceptibly that it was impossible to tell who had initiated it, their fingers became intertwined. Neither of them knew exactly what that meant, but they both had a feeling it was something good.

**The End :)**


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